Losing A Bet
by Zakura16
Summary: Draco loses a bet against Blaise and has to ask Harry out on a date. Chapter 1 with cross-dressing and chapter 2 without cross-dressing. Slash/Yaoi. Pairing: Draco x Harry. R&R Please.
1. Chapter 1

Disclaimer: I don't own Harry Potter or any of the characters. This is only for fun.

Warning: Cross-dressing

* * *

"Talk"

'Think'

Losing a bet.

"Come on Draco. You have to. You lost the bet." Blaise reminded Draco. "No way. I'm not doing it." Draco complained. "You have no choice Draco. You have to. Now go in there and ask him out already." Blaise said starting to get impatient. He pushed Draco towards the Great Hall's entrance. "No. I won't. I won't." Draco put up quite the struggle, but Blaise being longer and stronger won. The two entered the Great Hall and Blaise gave Draco a push in the direction of the Gryffindor table. Draco composed himself and strode confidently towards the golden trio.

Draco strode up to Harry and smiled smugly at him. The Golden trio glared at him, but he noticed that Harry's glare wasn't as sharp as the others and his smile turned into a smirk. "What do you want, Malfoy?" Ron demanded. "Nothing from you Weasel." Draco answered confidently. "Then why are you here? Get lost Ferret." Ron growled. Draco ignored Ron and turned his attention on Harry. "Pot-Harry." Draco corrected himself to use Harry's name and not surname. This surprised the students that herd him and even more so Harry.

"Yes?" Harry asked the blond curiously. "I was wondering if you would like to go on a date with me this Saturday?" Harry looked surprised before he registered what Draco said. "Um…Okay?" Harry asked uncertain. Ron made a sound of outrage. "Good I'll meet you outside Honeydukes Saturday at seven." With that Draco turned and left.

Ron turned and screamed on Harry so fast that he was unable to react. "Why the bloody hell did you say yes?" When Ron got no answer from Harry he got up and stormed off to Merlin knows where. Tears started gathering at the corners of Harry's eyes. He hated fighting with his friends. When Hermione saw this she grabbed his hand and pulled him to his feet. She dragged him out of the Great Hall and towards the Black Lake. They sat down under a tree near the Lake.

"Don't listen to Ron, Harry. He doesn't know how you feel about Malfoy." Hermione said calmly stroking Harry's hair, like a mother would to her child, with his head on her lap. "I just wish he'd listen before blowing up at me. This is not the first time he's done it. I don't know if I would be able to always forgive him when he does that, 'Mione." Harry said between sobs. Hermione sighed. "I know Harry. I know. I'm sick of his jealousy and temper as well." She spoke softly and calmly to try and calm him down.

"If you like or love Malfoy that's your choice. No one can decide how you feel. Not me, Ron or even Ginny has a say in what you feel." Hermione lectured. Harry gave a breathless laugh. "Thanks for your comforting lecture 'Mione. I feel better now." Harry sat up and wiped the tears from his face. "That's what friends are for." Hermione smiled at Harry before wrapping him up in a hug. "Everything's going to be okay, Harry. Ron will come to his senses."

"I hope so 'Mione. I really, really hope so." Harry said sadly. "Oh, Harry." Hermione hugged Harry tighter to her. She pulled away and gave Harry a bright smile. "So, a date with Malfoy?" Harry giggled at the mention of the date. "I can't believe I'm going on a date with the bloke I've had a crush on since second year." Harry giggled once more. Hermione gave him a playful smile. "So, what are you going to wear to the date? Dress? Skirt?" Harry gave her a playful shove before he stilled to ponder what she said. "Hey that's not a bad idea."

Hermione gaped at him before she broke out into a face splitting smile. "I have the perfect outfit! He won't be able to keep his hands off you." Harry gave Hermione a bright smile. "I can't wait to see the look on Draco's face when I show up in a skirt or dress." Harry broke into laughter when he imagined it. "Yes, that would be a sight to see." Hermione giggled. "And leave Ron to me. I'll sort him out. You just concentrate on your date with Malfoy."

"Thanks 'Mione. I owe you for this." "No problem, Harry. You know I'll do anything for you. I see you as my own brother and therefore I will always stay loyal to you." Harry gave her a big hug. "Thank you, 'Mione. At least I can always count on you." "There's no need to thank me Harry." Hermione said. "I know, but I want to."

Hermione broke the hug and got up. "Come let's get your outfit ready for your date." Harry eagerly got up and he and Hermione made their way towards Hogwarts. When they reached the portrait of the fat lady they gave the password and entered the Gryffindor common room. Harry looked around the room, but didn't see Ron anywhere. Harry let out a long sigh making Hermione look at him. "Don't worry about him Harry. Like I said I'll take care of him. Now let's go to my room so I can help you with your outfit for Saturday."

Harry nodded and followed Hermione to her room. When they entered her room she told Harry to sit on the bed while she goes to her closet to get the outfit. Harry sat down slowly on the bed and looked around. There was a LOT of books. On the desk, shelves and even stacks of books on the floor. He should probably not be surprised but he was. It was definitely a room of someone with high grades. Yeah there were the little things that a room of a girl should have but there were more books than anything else.

Hermione came back carrying the clothes she thought he should wear to his date with Draco. "Here. Get dressed so we could see if it will look good on you." Hermione placed the clothes in his arms and pushed him towards the bathroom that was attached to the bedroom. Harry nodded before entering the bathroom and closed the door. He didn't look properly at the clothes and got dressed.

When he was done he exits the bathroom and searched the room to find Hermione sitting on her bed waiting for him. "How do I look?" Hermione's head shot up when she heard his voice. Hermione let out a gasp when she saw how Harry looked. Harry got worried when she continued to gape at him. He started fidgeting the more she stared at him and finally asked, "What?" That seemed to snap her out of her trance and she broke into a bright smile.

"You look very beautiful, Harry. If I didn't know you I'd think you were a girl." Harry blushed at her praise. "Thanks 'Mione." Hermione smirked at Harry. "Malfoy won't know what hit him." Harry smiled shyly. "Do…Do you think he'll like it?" Hermione put her hands on her hips. "He'll love it and if he doesn't then he's an idiot. Saturday at five come to my room so you can get dressed and so that I can do your hair and make-up." "Alright 'Mione." Hermione pushed him back towards the bathroom so he could get dressed in his normal clothes.

Harry quickly got dressed and gave the clothes back to Hermione. "I'll see you Saturday at five. Goodnight 'Mione." "Goodnight Harry." She gave him a tight hug before he left. He slowly made his way towards his dorm room. When he entered he saw Ron, Seamus, Dean and Neville sitting by Ron's bed joking around. When they noticed him they went silent and wouldn't look at him. He quickly got dressed in his pj's and went to sleep.

* * *

Draco was waiting outside Honeydukes seven o'clock on Saturday. He was starting to get nervous the more minutes ticked by. He really likes Harry and hopes this date goes well so he could ask Harry to be his boyfriend. He fingered the bow of the gift in his pocket. He knows that you don't really give your date a gift on the first date but he wanted to make this day special for Harry. Draco was so deep in thought that he didn't see the figure approaching him. "Draco?" His head snapped up and he was speechless at the sight in front of him.

Harry's black hair that reached his shoulders was curled and his bangs pinned to the side. He wore black eyeliner and green eye shadow. His lips had lip-gloss on and he had a light blush dusting his cheeks. But the one thing that made him take a double take was his outfit. He wore a light green blouse with silver lining, a dark denim skirt, fishnet stockings and dragon hide boots that reached just below his knees.

Draco couldn't stop staring at the beautiful creature in front of him. "Draco?" Harry asked softly. The blush on his cheeks darkened more because of Draco staring intently at him. Draco snapped out of his daze and cleared his throat. "Shall we?" Draco held out his arm for Harry to take. Harry nodded his head before taking his arm. Draco placed his other hand on Harry's hand that lay on his arm.

Draco led them to Madam Paddifoot's Tea Shop. Harry pulled a face when he remembered the last time he was there with Cho. Harry took a deep breath and reminded himself that this was Draco and not Cho. When they entered the shop the bell over the door gave a tuneful tinkle to announce their presence. A waiter walked up to them and told them to follow. He led them to a table in the back near a window. When they took their seats the waiter gave them their menu's and told them to call him when their ready to order.

Draco took one of Harry's hands in his and laced their fingers. Harry blushed at the romantic gesture. "Why did you ask me out Draco?" Draco hesitated before deciding to tell Harry the truth. "I lost a bet with Blaise and he told me if I lose I have to ask you out. The reason he said that is because I've had a crush on you since second year." Harry blushed a deeper red when Draco said he has a crush on him. "Me too." He said softly.

Draco gave a small but genuine smile. Harry gave him a beaming smile in return. "So are you ready to order?" "Yes." Draco held up his hand and signalled the waiter over. Harry ordered a hazelnut latte and a slice of strawberry chocolate cake. Draco ordered a slice of cheesecake with a blueberry toping and jasmine tea. While they waited for their orders they made small talk. "Here you go." The waiter said giving them their orders and then leaving.

Draco took a bite from his cheesecake before he looked back at Harry. "Harry?" Harry looked up mid bite when he heard his name. He put down his fork and gave Draco his undivided attention. "Yes?" Draco looked hesitant for a second before asking, "Would…Would you like to be my boyfriend?" Harry's cheeks grew red and his eyes started watering. He gave Draco the biggest smile ever. "Yes! I'd love to be your boyfriend." Draco's smile was slightly bigger than the last one. "Good."

Draco took a sip from his tea and continued eating his cheesecake. He was so happy he could grab Harry and snog the living daylights out of him but held it in. He reminded himself that that will come soon and that he should be more patient. When they were done Draco paid and they left. They held hands while walking through Hogsmead. Neither boy wanting to end the date but soon they reached Hogwarts. Ron and Hermione waited outside the entrance for them. Draco stopped making Harry stop as well.

"This is where we say good-bye Harry." He said sadly. Harry could feel tears gathering in his eyes. Draco reached out and wiped the tears away with his thumps. Draco cupped Harry's face and leaned in. Their lips met gently and both moaned at the feeling. Draco swiped his tongue over Harry's bottom lip asking for permission to enter. Harry hesitantly opened his mouth to let it in. When their tongues met both moaned again. After snogging the living daylights out of Harry, Draco left leaving Harry with his friends.

Harry dazedly made his way towards his friends. "So Harry how was your date?" Hermione asked the still dazed Harry. "Good. He asked me to be his boyfriend." "Anaand?" "I said Yes." Hermione squealed and wrapped Harry in a tight hug. "I'm so happy for you Harry." When she let Harry go he noticed Ron for the first time. Ron cleared his throat before talking. "Sorry about yesterday mate. I didn't know you had a crush on Malfoy. If I knew I wouldn't have yelled at you. I'm really sorry."

Harry gave Ron a small smile. "It's okay Ron I forgive you. Just don't do it again." Ron nodded and the golden trio made their way towards the Gryffindor tower.


	2. Chapter 2

"Talk"

'Think'

Losing a bet.

"Come on Draco. You have to. You lost the bet." Blaise reminded Draco. "No way. I'm not doing it." Draco complained. "You have no choice Draco. You have to. Now go in there and ask him out already." Blaise said starting to get impatient. He pushed Draco towards the Great Hall's entrance. "No. I won't. I won't." Draco put up quite the struggle, but Blaise being longer and stronger won. The two entered the Great Hall and Blaise gave Draco a push in the direction of the Gryffindor table. Draco composed himself and strode confidently towards the golden trio.

Draco strode up to Harry and smiled smugly at him. The Golden trio glared at him, but he noticed that Harry's glare wasn't as sharp as the others and his smile turned into a smirk. "What do you want, Malfoy?" Ron demanded. "Nothing from you Weasel." Draco answered confidently. "Then why are you here? Get lost Ferret." Ron growled. Draco ignored Ron and turned his attention on Harry. "Pot-Harry." Draco corrected himself to use Harry's name and not surname. This surprised the students that herd him and even more so Harry.

"Yes?" Harry asked the blond curiously. "I was wondering if you would like to go on a date with me this Saturday?" Harry looked surprised before he registered what Draco said. "Um…Okay?" Harry asked uncertain. Ron made a sound of outrage. "Good I'll meet you outside Honeydukes Saturday at seven." With that Draco turned and left.

Ron turned and screamed on Harry so fast that he was unable to react. "Why the bloody hell did you say yes?" When Ron got no answer from Harry he got up and stormed off to Merlin knows where. Tears started gathering at the corners of Harry's eyes. He hated fighting with his friends. When Hermione saw this she grabbed his hand and pulled him to his feet. She dragged him out of the Great Hall and towards the Black Lake. They sat down under a tree near the Lake.

"Don't listen to Ron, Harry. He doesn't know how you feel about Malfoy." Hermione said calmly stroking Harry's hair, like a mother would to her child, with his head on her lap. "I just wish he'd listen before blowing up at me. This is not the first time he's done it. I don't know if I would be able to always forgive him when he does that, 'Mione." Harry said between sobs. Hermione sighed. "I know Harry. I know. I'm sick of his jealousy and temper as well." She spoke softly and calmly to try and calm him down.

"If you like or love Malfoy that's your choice. No one can decide how you feel. Not me, Ron or even Ginny has a say in what you feel." Hermione lectured. Harry gave a breathless laugh. "Thanks for your comforting lecture 'Mione. I feel better now." Harry sat up and wiped the tears from his face. "That's what friends are for." Hermione smiled at Harry before wrapping him up in a hug. "Everything's going to be okay, Harry. Ron will come to his senses."

"I hope so 'Mione. I really, really hope so." Harry said sadly. "Oh, Harry." Hermione hugged Harry tighter to her. She pulled away and gave Harry a bright smile. "So, a date with Malfoy?" Harry giggled at the mention of the date. "I can't believe I'm going on a date with the bloke I've had a crush on since second year." Harry giggled once more. Hermione gave him a playful smile. "So, what are you going to wear to the date? Dress? Skirt?" Harry gave her a playful shove. "No thanks 'Mione. I'm a boy not a girl."

Hermione huffed and pouted before her pout broke into a smile. "Well I still have an outfit that would look good on you and before you say anything. No it's not a girl outfit. I wanted to give it to you for Christmas but I'll give it to you now for your date." Harry gave Hermione a bright smile. "I can't wait to see Draco's face when I show up in something that's not too big for me." Harry broke into laughter when he imagined it. "Yes, that would be a sight to see." Hermione giggled. "And leave Ron to me. I'll sort him out. You just concentrate on your date with Malfoy."

"Thanks 'Mione. I owe you for this." "No problem, Harry. You know I'll do anything for you. I see you as my own brother and therefore I will always stay loyal to you." Harry gave her a big hug. "Thank you, 'Mione. At least I can always count on you." "There's no need to thank me Harry." Hermione said. "I know, but I want to."

Hermione broke the hug and got up. "Come let's get your outfit ready for your date." Harry eagerly got up and he and Hermione made their way towards Hogwarts. When they reached the portrait of the fat lady they gave the password and entered the Gryffindor common room. Harry looked around the room, but didn't see Ron anywhere. Harry let out a long sigh making Hermione look at him. "Don't worry about him Harry. Like I said I'll take care of him. Now let's go to my room so I can help you with your outfit for Saturday."

Harry nodded and followed Hermione to her room. When they entered her room she told Harry to sit on the bed while she goes to her closet to get the outfit. Harry sat down slowly on the bed and looked around. There was a LOT of books. On the desk, shelves and even stacks of books on the floor. He should probably not be surprised but he was. It was definitely a room of someone with high grades. Yeah there were the little things that a room of a girl should have but there were more books than anything else.

Hermione came back carrying the clothes she thought he should wear to his date with Draco. "Here. Get dressed so we could see if it will look good on you." Hermione placed the clothes in his arms and pushed him towards the bathroom that was attached to the bedroom. Harry nodded before entering the bathroom and closed the door. He didn't look properly at the clothes and got dressed.

When he was done he exits the bathroom and searched the room to find Hermione sitting on her bed waiting for him. "How do I look?" Hermione's head shot up when she heard his voice. Hermione let out a gasp when she saw how Harry looked. Harry got worried when she continued to gape at him. He started fidgeting the more she stared at him and finally asked, "What?" That seemed to snap her out of her trance and she broke into a bright smile.

"You look very beautiful Harry. With those clothes on you look like a different person." Harry blushed at her praise. "Thanks 'Mione." Hermione smirked at Harry. "Malfoy won't know what hit him." Harry smiled shyly. "Do…Do you think he'll like it?" Hermione put her hands on her hips. "He'll love it and if he doesn't then he's an idiot. Saturday at five come to my room so you can get dressed and so that I can help you with your hair." "Alright 'Mione." Hermione pushed him back towards the bathroom so he could get dressed in his normal clothes.

Harry quickly got dressed and gave the clothes back to Hermione. "I'll see you Saturday at five. Goodnight 'Mione." "Goodnight Harry." She gave him a tight hug before he left. He slowly made his way towards his dorm room. When he entered he saw Ron, Seamus, Dean and Neville sitting by Ron's bed joking around. When they noticed him they went silent and wouldn't look at him. He quickly got dressed in his pj's and went to sleep.

Draco was waiting outside Honeydukes seven o'clock on Saturday. He was starting to get nervous the more minutes ticked by. He really likes Harry and hopes this date goes well so he could ask Harry to be his boyfriend. He fingered the bow of the gift in his pocket. He knows that you don't really give your date a gift on the first date but he wanted to make this day special for Harry. Draco was so deep in thought that he didn't see the figure approaching him. "Draco?" His head snapped up and he was speechless at the sight in front of him.

Harry's black hair framed his face perfectly and he had a slight blush dusting his cheeks but the one thing that made him take a double take was his outfit. He wore skin tight black skinny jeans, an emerald green shirt with silver embroidery and black dragon hide boots. He was truly a beautiful sight to see.

Draco couldn't stop staring at the beautiful creature in front of him. "Draco?" Harry asked softly. The blush on his cheeks darkened more because of Draco staring intently at him. Draco snapped out of his daze and cleared his throat. "Shall we?" Draco held out his arm for Harry to take. Harry nodded his head before taking his arm. Draco placed his other hand on Harry's hand that lay on his arm.

Draco led them to Madam Paddifoot's Tea Shop. Harry pulled a face when he remembered the last time he was there with Cho. Harry took a deep breath and reminded himself that this was Draco and not Cho. When they entered the shop the bell over the door gave a tuneful tinkle to announce their presence. A waiter walked up to them and told them to follow. He led them to a table in the back near a window. When they took their seats the waiter gave them their menu's and told them to call him when their ready to order.

Draco took one of Harry's hands in his and laced their fingers. Harry blushed at the romantic gesture. "Why did you ask me out Draco?" Draco hesitated before deciding to tell Harry the truth. "I lost a bet with Blaise and he told me if I lose I have to ask you out. The reason he said that is because I've had a crush on you since second year." Harry blushed a deeper red when Draco said he has a crush on him. "Me too." He said softly.

Draco gave a small but genuine smile. Harry gave him a beaming smile in return. "So are you ready to order?" "Yes." Draco held up his hand and signalled the waiter over. Harry ordered a hazelnut latte and a slice of strawberry chocolate cake. Draco ordered a slice of cheesecake with a blueberry toping and jasmine tea. While they waited for their orders they made small talk. "Here you go." The waiter said giving them their orders and then leaving.

Draco took a bite from his cheesecake before he looked back at Harry. "Harry?" Harry looked up mid bite when he heard his name. He put down his fork and gave Draco his undivided attention. "Yes?" Draco looked hesitant for a second before asking, "Would…Would you like to be my boyfriend?" Harry's cheeks grew red and his eyes started watering. He gave Draco the biggest smile ever. "Yes! I'd love to be your boyfriend." Draco's smile was slightly bigger than the last one. "Good."

Draco took a sip from his tea and continued eating his cheesecake. He was so happy he could grab Harry and snog the living daylights out of him but held it in. He reminded himself that that will come soon and that he should be more patient. When they were done Draco paid and they left. They held hands while walking through Hogsmead. Neither boy wanting to end the date but soon they reached Hogwarts. Ron and Hermione waited outside the entrance for them. Draco stopped making Harry stop as well.

"This is where we say good-bye Harry." He said sadly. Harry could feel tears gathering in his eyes. Draco reached out and wiped the tears away with his thumps. Draco cupped Harry's face and leaned in. Their lips met gently and both moaned at the feeling. Draco swiped his tongue over Harry's bottom lip asking for permission to enter. Harry hesitantly opened his mouth to let it in. When their tongues met both moaned again. After snogging the living daylights out of Harry, Draco left leaving Harry with his friends.

Harry dazedly made his way towards his friends. "So Harry how was your date?" Hermione asked the still dazed Harry. "Good. He asked me to be his boyfriend." "Anaand?" "I said Yes." Hermione squealed and wrapped Harry in a tight hug. "I'm so happy for you Harry." When she let Harry go he noticed Ron for the first time. Ron cleared his throat before talking. "Sorry about yesterday mate. I didn't know you had a crush on Malfoy. If I knew I wouldn't have yelled at you. I'm really sorry."

Harry gave Ron a small smile. "It's okay Ron I forgive you. Just don't do it again." Ron nodded and the golden trio made their way towards the Gryffindor tower.


End file.
